Triphenylphosphine → HCID 57937606, compound

Participants

Reaction Steps

To a slurry of methyl 3-hydroxy-5-{5-[(trifluoromethyl)oxy]-1H-benzimidazol-1-yl}-2-thiophenecarboxylate (0.71 g, 2.0 mmol) and (1S)-1-(2-chloro-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}phenyl)ethanol (Intermediate 17, 0.63 g, 2.2 mmol) so DCM (20 mL) was added triphenylphosphine (1.1 g, 4.0 mmol) and di-tert-butylazodicarboxylate (0.92 g, 4.0 mmol). The clear, yellow solution was stirred for 1 h, then silica gel (5 g) was added. The volatiles were evaporated under reduced pressure and the residue was purified by flash column chromatography (0 to 50% EtOAc:DCM) to give 1.1 g (1.8 mmol) of the methyl 3-{[(1R)-1-(2-chloro-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}phenyl)ethyl]oxy}-5-[5-(1-methyl-1H-pyrazol-4-yl)-1H-benzimidazol-1-yl]-2-thiophenecarboxylate which was dissolved in THF (15 mL). 1 N tetrabutylammonium fluoride in THF (1.8 mL, 1.8 mmol) was added. After 10 min, silica (3 g) was added, the volatiles were evaporated under reduced pressure and the residue was purified by flash column chromatography (0 to 70% EtOAc:DCM) to afford 0.36 g (47%) of the title compound as a solid. 1H NMR (400 MHz, CD3OD): δ 8.48 (s, 1H), 7.63 (s, 1H), 7.40 (d, J=8.97 Hz, 1H), 7.30 (d, J=8.79 Hz, 1H), 7.13 (m, 2H), 7.0 (s, 1H), 6.8 (d, J=7.51 Hz, 1H), 5.95 (q, J=6.17 Hz, 1H), 3.88 (s, 3H), 1.68(d, J=6.23 Hz, 3H).

Provenance & Evidence